The Worst Dating Mistakes

This week's letter comes from a guy who waited two months to call an ex-colleague, forced a kiss on her on the first date and then discussed negative topics on the second.

reader's question

Hey Doc,

I've been wanting to write you and thank you for "The System." My buddies think I'm crazy for listening to your advice, but here we go.

Several weeks ago my coworker Angela left the company we worked for and got another job. After a few weeks, she e-mailed me with her new work phone number and her home phone number and suggested we get together.

I didn't set up a date for about two months and then called Angela on a Friday night for coffee. Bad move on my part, I now realize, but I was feeling desperate.

coffee and a kiss

We went out to a nice coffee shop here in Ventura. After ordering, we sat down and talked. An hour later I stood up and said, "Let's go." She asked why, and I answered that we were going to a club. She was surprised, but took me up on the idea. We danced for a couple of hours and then I drove her home. On the way she said she had a good time and that she enjoyed herself.

Once at her place, I jumped out of the car and opened her door. She said thanks, but before she got to her gate, I pulled her back for a kiss. At first she gave me her cheek, but when I went for her lips, she reciprocated.

things got negative

I waited until the following Tuesday and asked her out for Thursday, for a sandwich and some pool after work. At the sandwich shop we had a good conversation going, but when we drove to the pool hall, it went awry. We started talking about some negative stuff — why she left her job — and this seemed to get her down.

We did shoot a little pool and stayed out until 9:30, but it was strained. I drove her home and kissed her. She said she had fun and all was well — or so I thought.

I called Angela the next Tuesday and again invited her out, for Chinese food and drinks. She said no, and that she was busy. She didn't make a counteroffer. I haven't heard from her since, and that was a couple of weeks ago.

Doc, I'm completely bummed. What did I do wrong? The relationship seemed to go south on the basis of that one lousy conversation. Is that possible? Do you think I should ask Angela out again? If so, how should I go about it?

Stevie — who's scratching his head over what he said wrong

doc love's answer

Hi Stevie,

If your buddies think you're crazy, this means you've been force-feeding them "The System." Only when they come to you in pain can you give them advice. But you're like a guy who suddenly doesn't drink anymore, and now he's seen the light and decides he's going to save the world.

Your friends don't care and you waited way too long to contact this girl...